Well Hello Magic: A Disney Planning & Experience Podcast
Jessica Mickelson is the voice behind Well Hello Magic, a Disney-loving mom of four, former therapist, podcast host, content creator, and trusted expert in Disney vacation planning for families, moms, and first-time travelers. She is also part of a proud military family, bringing an added layer of understanding to planning trips around real-life schedules, budgets, and seasons of change.
A lifelong Disney fan raised on Main Street magic and Mickey-shaped memories, Jessica helps families confidently plan trips to Walt Disney World, Disneyland, and Disney Cruise Line without overwhelm, burnout, or blowing the budget. Her approach to Disney trip planning focuses on realistic expectations, thoughtful strategies, and creating meaningful experiences that work for real families.
As a mom who has done Disney with toddlers, teens, grandparents, large groups, and multigenerational families, Jessica shares real-world Disney planning advice rooted in emotional insight and hands-on experience. From stroller-friendly itineraries to thrill-ride strategies, from solo trips to girls’ weekends and group vacations of 14 or more, she gives listeners the tools to plan Disney vacations that feel magical and manageable.
On the Well Hello Magic podcast, Jessica shares Disney vacation tips, park planning strategies, Lightning Lane guidance, event guides like Mickey’s Not-So-Scary Halloween Party and Mickey’s Very Merry Christmas Party, and honest reflections on the emotional side of Disney travel. Episodes feature expert guests and fellow Disney-loving moms who understand the balance between preparation, flexibility, and enjoying the moment.
Beyond the podcast, Jessica creates daily Disney and family travel content on Instagram and YouTube, blending humor, helpful hacks, and heartfelt storytelling into practical videos for Disney travelers at every stage of life.
Well Hello Magic: A Disney Planning & Experience Podcast
113: Behind the Magic - Guest Creator Brittany from Travels by Brittanyb
Today’s episode is extra special because we’re welcoming back one of the original Well Hello Disney family members—Brittany B! If you’ve been here since the early days (we’re talking 2022, under 1,000 followers), then you might remember when Brittany was planning her very first Walt Disney World trip with her two young kids. What started as a mom planning her first Disney vacation has turned into something truly magical.
Fast forward three years, and Brittany has gone from first-time Disney mom to full-blown travel agent and content creator, helping other families confidently plan their own magical vacations. In this episode, we sit down mom-to-mom and dive deep into the realities of traveling to Disney with little kids—because it’s magical, but it’s also a lot.
We cover everything from:
- Navigating Walt Disney World with young kids
- What it’s really like taking little ones on Disney Cruise Line
- Handling overstimulation, exhaustion, and big emotions
- Stroller life—how much we need them, love them, and rely on them
- Tips for enjoying the parks without the pressure to “do it all”
This conversation is packed with real-life experience, practical advice, and reassurance for parents who want the magic without the meltdown. We also chat about our shared love for Disney, how Brittany’s journey has evolved, and what we’re most excited about for the future of Disney travel.
So grab a pen and paper—because you’re going to want to take notes.
If you’re planning a trip to Walt Disney World or a Disney Cruise with young kids, this is the episode for you.
Guest: Brittany B
✨ OG Well Hello Disney family member
✨ Disney-loving mom, content creator & travel advisor
✨ Specializes in family-friendly Disney vacations
Find Brittany on Instagram:
📸 @travelsbybrittanyb
👉 https://www.instagram.com/travelsbybrittanyb/
Travel Agent Information:
✈️ Independent Travel Advisor
🏰 Specializing in Walt Disney World, Disney Cruise Line & family travel
📩 Contact Brittany via Instagram DMs for personalized trip planning, tips, and quotes
What We Cover in This Episode:
- Disney Cruise Line with toddlers & young kids
- Walt Disney World park strategies for families
- Managing overstimulation and tired kids
- Stroller must-haves and survival tips
- Mom-to-mom encouragement and realistic Disney expectations
- What’s coming next in Disney travel
🎧 Don’t forget to subscribe, leave a review, and share this episode with a fellow Disney mom who needs a little extra magic in their planning.
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